“It Wasn’t Just Character. It Was Circumstances.”

John Swansburg and his editor Jessica Winter talk about how his history of the self-made man came to life.

Illustration composite by Slate. Portraits by Charlie Powell and background by Happy Menocal.

This story is part of a special Slate Plus feature package on “The Self-Made Man.” Be sure to check out the other Slate Plus exclusives related to John Swansburg’s history of the self-made man, including a full audio version of the piece and an inside look at how the self-made men profiled in Swansburg’s story see their sons.

As a member of Slate Plus, you’ll get access to exclusive podcasts—including this conversation between John Swansburg, Slate’s deputy editor and the author of “The Self-Made Man” and Slate senior editor Jessica Winter, who edited his longform piece.

In this behind-the-scenes podcast, Swansburg chats about the origin of the piece, the long process of research and reporting, and how Benjamin Franklin stressed him out.

Here is the transcript of the conversation:

Jessica Winter: Hello, I’m Jessica Winter, a senior editor at Slate, and I’ve recently been lucky enough to work with my colleague John Swansburg on his Fresca, which is our in-house term here at Slate for longform reporting and writing projects where our writers and editors can step off the daily hamster wheel for a month or so and take a big bite out of a single subject or story.

John, who is also the deputy editor of Slate, has written a piece on the notion of the self-made man, that iconic figure who pulls himself up by the bootstraps and goes from rags to riches through pluck, ingenuity, and sheer hard work. The idea of the self-made man is a cherished part of the American identity—as John’s piece details—and of American history and literature.

But as John reveals in his piece, there has often been a great chasm between the idea and the reality. John traces the mythology of the self-made man through several different characters, ranging from Benjamin Franklin to Horatio Alger to the contemporary fashion retailer and self-made woman Sophia Amoruso, and even to John’s own father, the real estate baron Jack Swansburg. Can we call him a real estate baron?

John Swansburg: I think he would be embarrassed if we did, but I think we should anyway.

Winter: So this is a deeply researched and utterly fascinating piece that is available for Slate Plus members to read now, and John is joining us today for a special Slate Plus podcast. Hello, John.

Swansburg: Hey Jessica, thanks so much for having me. And first off, thank you so much for editing this monster of a piece.

Winter: It’s not a monster.

Swansburg: Well, it’s very long and it’s very complicated and you were a fantastic cheerleader throughout the process. I’m really grateful to you and I wanted to say that on the air. So everyone can hear that to the extent this piece is good, it’s largely thanks to Jessica’s editing.

Winter: That’s not true, and if it is a monster, it’s a beautiful monster in part because John’s very talented wife, the artist Happy Menocal has done watercolor portraits of all the characters in the piece.

Swansburg: Indeed, I was able to get my lovely wife to do those paintings, which was very exciting. Keep the piece in the family.

Winter: So let’s begin at the beginning. How did you first land on the idea of writing on the self-made man. What was the first kernel of the project?

Swansburg: That’s a good question. It’s an idea I’ve been kicking around for a while, so in a way it’s hared to pin down the exact origin. As I write in the piece, and as you just indicated, my father himself is a self-made man.

So I’ve always been interested in the subject of the self-made man because I think when you’re the son of a guy, who, in my dad’s case was born into a working-class family outside of Boston and came up as a roofer, and sort of due to his hard work and ingenuity made something of himself—you are naturally in the subject. So I had that personal connection to the story, but I never really found a way to get purchase on it, I had thought about writing on it for a few years and I never really knew how.

And then, actually gratifyingly enough, on my previous Fresca, which I wrote about a Civil War general turned novelist named Lew Wallace, I got to go to this academic conference at Rutgers, it was an incredibly dorky event, it was like a full day conference about Ben Hur—his greatest novel, the one that people know him for and that later became a movie—and one of the literature professors at this conference pointed out the talk had sort of turned to why Ben Hur was such a best-selling success in the 1890s and this professor was enumerating all of the reasons and one of the reasons that he came up with was that well, you know, there’s actually sort of this Horatio Alger story embedded in Ben Hur. And I thought to myself, “Oh, that’s so interesting,” and I hadn’t sort of thought that a Horatio Alger or Alger-esque stories might appear in another part of American literature.

And that kind of got me thinking, “Oh, where does the self-made man show up besides Alger stories?” It kind of lit the fire for me a bit, and I said that could be maybe my next Fresca kind of investigating where does this idea come from? Did it start with Alger, did it start somewhere earlier? And so I kind of liked that it was my previous Fresca that kind of pointed me in the direction of finally writing about this subject that I’d been interested in for a long time.

Winter: At least chronologically, your starting point is Benjamin Franklin—

Swansburg: Right.

Winter: And as your concerned and caring editor, I started really disliking Benjamin Franklin because he was stressing you out.

Swansburg: Benjamin Franklin stressed me out for this piece. It turned out that—probably I should have known—Benjamin Franklin invented the self-made man like he invented so many other things in the world. I actually love Benjamin Franklin as a character, as a thinker, as a writer, but the reason that he was giving me fits was that he’s just such a wonderfully complicated figure. And he’s obviously someone of momentous import to American history and American literature, and has been written about so much that I feel like mastering Ben Franklin is something you could spend a lifetime trying to do and never do. And he was an important character in my story, but he’s one of I think eight characters, so trying to sort of budge my time—I had a four-week sabbatical in which to research this piece—trying to wrap my mind around Franklin, feel comfortable enough to write about him, it was really hard.

But he is maybe my favorite character in the piece, other than my own father, obviously, because he is just so fun to read. The foundational text of the self-made man methodology is Franklin’s own autobiography, which is a book I confess I’d never read, I’m embarrassed by that, I think every American should read it. It’s short. If nothing else comes of this Fresca, then if people go out and buy Franklin’s autobiography and read it, then that would make me a very happy writer.

Winter: John is here to shame you. You haven’t read—

Swansburg: No, I’m just here to sell books for Ben Franklin. So Franklin lived the self-made story, he certainly wasn’t the first human being on the planet to “emerge from obscurity” as he put it, but he was sort of the first American to start so low. He was the 10th son of a poor candle- and soap-maker, back then they made candles and soap out of tallow, which is very smelly, it was a very unpleasant business to be in, and Franklin obviously grows up to be quite a wealthy printer by dint of his industry and smarts and ultimately an incredibly important figure and obviously in the founding of the United States and an important scientist.

So he lives like this incredible story of going from complete obscurity, born on Milk Street to this poor father, and then he’s arguably one of the most, one of probably three or four of the most famous people in the world at the time of his death. So his own telling of that story has set the self-made mythology in motion.

Winter: And, of course, he’s one of eight characters, as you mentioned, and several of our recent Fresca project have focused on a single protagonist: Josh Levin wrote on Linda Taylor, the notorious “Welfare Queen,” David Haglund recently wrote on the former NBA player Delonte West. Your piece is different, John, because you’re focusing on several different people; some of them are long gone, some of them are still with us, some of them are close to you, some of them you just met. But also, in a larger sense, your protagonist is not a person, your protagonist is sort of an idea. What kinds of challenges did that present?

Swansburg: Big ones, that was a really tough thing. I think whenever a Slate staffer goes out on one of these Fresca projects, the first day is really terrifying, because you realize, OK, now I actually have these four weeks in which to produce this great piece of journalism, hopefully. And in a way, four weeks, when you think about it in the abstract, seems like a nice, long break from the daily grind, but actually it’s not very much time at all.

Particularly if you’ve taken on an ambitious project like Josh’s project on the “Welfare Queen.” And so I remembered that from my Lew Wallace Fresca, being like OK, the first day is kind of scary, because you don’t know can I actually do this, can I pull this off? Is this really the idea for me? But this time around, the first four days were completely nightmarish. I like—

Winter: I can confirm this, I saw John the evening of day four.

Swansburg: You saw me the evening of day four, I feel like I was a wan, shell of my normal self.

Winter: You fronted so well. You kept saying that you were freaked out, but you seemed fine.

Swansburg: See, Jessica and I saw each other at like a swank magazine awards dinner, so I was wearing a nice suit, so I probably managed to not look as haggard as I actually was. I really kind of tore my hair out the first four days. In large part because I realized I’d taken on what you just described, that I was trying to write the kind of biography of an idea. And I love when writers pull that off, I think it’s incredible, but it’s really difficult. And I’m not sure that it necessarily plays to my strengths.

I sort of like telling stories, and in the Lew Wallace Fresca, I sort of told a man’s story, although it was also the story of a novel. And I feel like what was so scary to me those first four days is that I didn’t know how to go about telling the story of an idea. And actually David Plotz, I talked to him on I think the Wednesday of that week, and he offered this insight that proved to be really crucial.

Winter: David Plotz, the, until very recently, editor-in-chief of Slate.

Swansburg: Correct. He said to me, “You obviously are writing a story about an idea, but you’re also writing a story about people, find the people who illustrate the evolution of this idea that you want to show, and make it about them and let the people kind of lead the story along.” And that seems like kind of an obvious observation, but it hadn’t occurred to me, and the second he said that, I was like, “Oh, OK, who would those people be?”

Like if I had to make a list of people, I know I had to start with Franklin, he’s the undisputed founder of the American self-made ideal, if I want to plot the course of the idea, from Franklin up to the present who would those people be? And that was like, OK, let me think who would those people be? And there were certain stops along the way that I already knew. So I knew that I wanted to get to Andrew Carnegie to be the person who represented what the ideal became in the Gilded Age, for various reasons, one because he wrote his own autobiography which was influential, in which he talks about his own self-made ideals.

I knew I wanted eventually to get to my own father who was born in the 1950s and represented kind of a post-war representation of this story of bootstrapping. But I didn’t know who some of the stops along the way would be, so that was how I started my research: OK, who was a self-made man of the first half of the 19th century, Franklin dies, his autobiography was published shortly after his death in 1794, and that book becomes wildly popular in the young republic, and all these young farm boys read it and say, “Oh, he was just a candle-maker’s son in Boston and he became the most famous man in America, and one of the most famous people in the world. I could do that.”

And so I said, all right, who were those boys who were reading this book, where did they go, what did they do, how can I find an illustrative person to tell that story. So once I started thinking about it as a story about an idea that was lived by people, then it felt like I could do it.

Winter: Right. What established notions that you might have had about the self-made man, how did those change or evolve as you got deeper and deeper into your research and you got to know all of these people along the way?

Swansburg: Well, I guess the other thing I would say that made me feel like I hadn’t assigned myself the dumbest story idea in the history of longform journalism was this discovery that the self-made ideal isn’t a monolithic idea.

I guess I was afraid that there was this version we all kind of know because it’s out there in the ether, and the idea is you can be born poor in America and if you work hard enough, this is the land of opportunity, and people who want it badly enough and are willing to put in the sweat will get what they want. I think we can all recognize that that’s an ideal, it’s certainly not true for everybody, and I talk about the distance between the mythology and the reality in the piece, but I guess I was afraid on those first days that that was just the idea and Franklin inaugurated the idea and here we are today and we still believe it, kind of weirdly because it doesn’t happen that often, and yet we still buy into it.

But what I’ve found when I started doing research, and I’m very much indebted to a pair of academics, one named John Cawelti and the other is names Irvin Wiley who wrote books in the ’50s and ’60s that are sort of academic studies of the self-made literature, particularly of the 19th century, and reading those books, it became clear to me that no, the self-made ideal really changed over time. It meant one thing to Franklin, and he expressed it a certain way, it meant something different to the generation that came right after Franklin. For instance the self-made mythology right after Franklin’s death changed in this interesting way. Franklin had sort of stressed the importance of hard work, and he talked a bit about temperance and keeping your nose to the grindstone, but that was sort of less important.

In the immediate aftermath of his death, as the country was experiencing this exploding economic growth, the self-made ideal became sort of like a didactic story that was told to these young farm boys, who were moving to the city to explore the opportunities that were in places like Boston and New York and Philadelphia. And they were encouraged to work hard, but more than that, they were encouraged to sort of keep their noses clean and not go to the taverns, not go to the theater, not take up with women of ill repute.

There was this fear that all these pure farm boys who had been raised in Vermont, you know, farming rocks or whatever, would move to the fleshpots of New York City and all of a sudden they would go there to seek their fortune but in fact they would find ruin because their morals would be compromised. So the self-made man of the first half of the 19th century wasn’t even really like a businessman.

When you read the self-made stories from that period, it’s funny because they’re not really like about business, they don’t tell you anything about how this dry goods merchant did really well. It’s all about how well, he was the most pious, rectitudinous guy, he never so much as looked at a woman of ill repute, he never even went to the parts of town where they lived. That was the story of the self-made man then. And then it changes again in the Gilded Age, and so the ideal changes over time in this way that I found really interesting. So that was sort of the biggest discovery: that there isn’t one self-made man, there were all these different avatars of the idea. And that sort of became the thrust of the piece, finding how the story changed.

Winter: One of the nuggets, many nuggets, I liked in the piece is Andrew Carnegie: not a workaholic.

Swansburg: No, he’s not. That was a really fun discovery. For the first hundred years or so of the self-made ideal, working hard was a very important part, and I think today we think working hard is being a very central virtue of the self-made man, but Carnegie himself didn’t work that hard.

I mean, that’s not to say he wasn’t industrious in his own way, he didn’t luck into his wealth, he was certainly lucky in certain ways, but if he could get done everything he needed to get done by lunchtime and then spend the rest of the day listening to a concert or reading a novel or going to the country and meeting friends, he was very happy to do that.

And he didn’t shy away from saying that. I think he knew that for him, it hadn’t been about working 18-hour days to reach the success that he reached. He did it more though ingenuity and somewhat ruthless pursuit of wealth.

Winter: Right, early pioneer of work-life balance.

Swansburg: He was, you know, it was slightly easy for him at a certain point to have a work-life balance because he had accumulated such incredible wealth through a series of crony capitalistic deals that once he mad his millions, it was easy for him to knock off at lunch and still be a titan of industry. Earlier in his career, he sort of did work harder, but he was sort of in the right place at the right time in Pittsburgh and a lot of things kind of landed in his lap.

Winter: I want to talk to you about your dad, who becomes such a vivid figure in the piece, and I loved getting to know him, and getting to know part of his slang lexicon. I won’t spoil any of it for our readers, but I feel as though my vocabulary is richer for having met him through your writing.

Swansburg: That makes me very happy.

Winter: Did working on this project change—I know it changed how you viewed this ideal that we as Americans hold up so high, but did it change how you actually saw your dad?

Swansburg: It did. I’ve always looked up to him for having succeeded the way that he did. For having been born into these relatively meager circumstances and having enjoyed the success that he did. He’s one of these guys who sort of have a preternatural ability to see opportunity where other people don’t and he has just a wonderful, swash-buckling kind of way of walking through the world. I admired that. That apple fell very far from the tree. I’m not a good businessperson, I don’t have that cast of mind, so it’s just so strange to me as someone who is a journalist, is kind of bookish, is a terrible negotiator, to look and see that I came from this guy who has all these skills that I don’t possess. So I always sort of really—

Winter: You have swash-buckled, though.

Swansburg: Oh, yeah, I’m a total swash-buckler, just in my own way. As a kid, I really looked up to him for having all of those qualities that I didn’t have. One thing I realized was I caught myself in the course of thinking through this piece, mythologizing my dad the way that I think all Americans had kind of mythologized the self-made man. I told myself that he lived this version of the self-made story.

His version of the story turned out to be more complicated that I thought. And in the way that you kind of have the sense of what your parents did before you arrived in the world, but it’s somewhat rare to sit them down and actually get them to tell you their story. One of the great pleasures of this project was I actually arranged to interview my dad as if he were a source for a story, like any other source. I spent a whole afternoon with him. I took the train to Boston and he picked me up and we basically took a driving tour of his career. So we started in Winthrop, the town outside of Boston where he grew up, and then we drove through Chelsea and Charlestown and Somerville and all of these places that are actually now, because of the way Boston has changed, relatively nice places—Chelsea, not so much—but kind of this rusted, industrial ring outside of Boston, which is where my dad started out as a roofer, but ultimately bought a bunch of really ugly buildings that he called pigs, these ugly, industrial spaces.

And he took me for a tour of a bunch of these industrial buildings. So he would say, oh, this one right here, and then he told me the story of the deal and how he somehow managed to pull the wool over someone’s eyes and managed to get it for half of what it was worth. I had always loved hearing my dad tell these stories because each one is crazier than the next. There was one sort of chapter in his story that I had never sort of got, which is how he went from being a roofer—just a guy getting paid an hourly wage to put asphalt on a roof—to being a guy who could buy a pig. Now, even a pig was an ugly building in an undesirable part of Boston in the 1960s, but it was still, we’re talking about buildings that were 70,000 square feet. The average guy who’s laying asphalt on a roof doesn’t have the means to make that acquisition, so how did he get from point A to point B?

So he told me the story about how he went from being a roofer and how he ultimately opened up his own roofing shop and then he built his own roofing company into a very profitable concern, and sold that. And then he was on his way, but the aspect of that chapter that I didn’t know that was very surprising, and I talk about that in the piece, is that he arrived in the roofing business in this very interesting moment where it was possible for an upstart like himself to succeed. He didn’t start his business because he saw an opportunity, he started his business because some other guy went bankrupt and he was able to get the equipment for cheap. So, in his words, he was like, “Fuck it, I’m going to go and give this a shot for myself. I don’t want to work for anyone else, I’m going to pay out my own shingle.”

So he started this small company, and somewhat by luck, it was a moment where roofing technology was changing, the materials were changing, the asphalt had been what you roofed with before, now it was going to rubber, and that change seems like kind of a banal thing, but it turned out to mean that you could be a very small operation, you could bid on a very big project and underbid some of the bigger players, and you could go in with a small crew of guys and go in and do a job and do it well. And so the circumstances of his success were somewhat created by these extrinsic events, just a change in roofing material. And that was something I had never known, and it complicated his self-made story for me. It wasn’t just he imposed his will on the world, it was that he did that at a moment where it was possible to succeed for these other reasons.

Winter: But that’s such a mobius strip, isn’t it? Whether you’re talking about Andrew Carnegie or Jack Swansburg, you can say someone was lucky or someone was in the right place at the right time, or a happy accident befell someone, but why were you in that place at just the right time, what kind of pluck and ingenuity and foresight and just horse sense factors into that?

Swansburg: Right, I think that’s absolutely, it’s the question I kept coming back to with all of the characters in this story. Sophia Amoruso—who is the lone woman in the story—she’s a 30-year-old woman who started a company called Nasty Gal, that’s her online retailer and it sells clothes, primarily for I think twentysomething women and she started selling vintage clothes on eBay. And she is a similar kind of thing. She got to eBay at a moment where there were a lot of other vintage sellers, but she had this idea that instead of just draping her Golden Girls tracksuit like on a sad hanger and taking it in a dimly-lit family room, she got cool-looking girls, she actually styled them well, she got a professional photographer, or took her own photographs and staged them in a way to make the clothes look awesome and made the person who might bid on them seem more interested, because they’re buying not just the item, but a look.

And she had that idea in a moment in eBay history, social media history, that was conducive to building success out of what seams relatively obvious idea, like make your clothes look better and they’ll fetch more money on an auction site. But she did, she had the ingenuity to style the shots that way, she had the wherewithal and the idea to friend a bunch of people on MySpace, which was the then dominant social media platform in 2005 when she got started, or 2006. She made it work. So is her success a product of having arrived on the Internet at the exact moment to exploit her idea or is it was she going to be a success no matter what it was just a matter of finding the outlet for that for her talent and her stick-to-it-iveness? I don’t know.

I guess the point to it in my piece was that when I would tell my dad’s story, before I wrote this piece, I told it like a simple, self-made man story. My dad succeeded because he had the work ethic to put 400 degree asphalt on the roofs of Chelsea, Massachusetts, for years until he saved enough money, then he started his own business, and he worked so hard at that business that he made it a success and then the rest is history. The story is more complicated than that. So I sort of mythologized it.

I guess the distinction is in the self-made myth making, the story becomes only about a character. It’s like the star had these attributes and he imposed those attributes on the world, and the world repaid him with wealth. Whereas what I found with my dad’s story and the story of Carnegie and most of the people in my story: Yes, they had the right character attributes, they all were hard workers, expect for maybe Carnegie, they all had ingenuity, they all had smarts, but they also all arrived in their industries at a moment that lent itself to their success. The world had something to do with it, it wasn’t just that they had the right attributes. So it wasn’t just character, it was circumstances I guess.

Winter: Has your dad read the piece?

Swansburg: He has not read it yet, although he has expressed a great desire to read it.

Winter: I’m looking forward to hearing his feedback, should he decide to share.

Swansburg: Me too. I’m slightly terrified but yes, also excited.

Winter: All right, well the piece is available a little early for Slate Plus members, and there will be some extra perks: John will be publishing another essay and we’ll also have a recording of John reading the piece. It’s a great achievement and I hope Slate Plus members will check it out. John, thanks so much.